Matt Verlaque – Humor Around one’s own Stories

Matt Verlach Discusses Humor and Leadership in Remote Work Environments

Matt Verlaque is an experienced CEO and entrepreneur with a remarkable journey from being a firefighter to establishing and leading a successful SaaS company. Transitioning from over a decade in the fire service in Maryland and Virginia, Matt co-founded his first SaaS company in 2016, which he led to a prosperous acquisition in 2020. Currently, he serves as the CEO of SaaS Academy, where he mentors and trains over 500 SaaS founders. Matt balances his professional commitments with his roles as a devoted husband and father of three, and he enjoys weightlifting, running, and biking in his free time.

Episode Summary:

In this engaging episode of “Humor in the C-suite,” Kate Davis sits down with Matt Verlaque, a former firefighter turned SaaS CEO. Matt shares his fascinating journey from battling flames to building tech startups, highlighting the importance of humor and camaraderie in his transition from the firehouse to the boardroom. The episode delves into how Matt accidentally stumbled upon software entrepreneurship while helping a colleague with his CrossFit gym’s operations and how that led to the creation of a successful SaaS company.

Through Matt’s narrative, listeners get an inside look at SaaS Academy’s mission and culture, emphasizing the use of humor as an essential tool in leadership and team building. Matt discusses how humor helps maintain a positive atmosphere in a high-stakes environment, and contrasts the use of humor in client interactions versus internal team dynamics. They explore the role of humor in overcoming challenges, building deeper relationships within remote teams, and enhancing overall effectiveness and well-being.

Key Takeaways:

  • Transition and Growth: Matt’s journey from a firefighter to a successful entrepreneur in the SaaS industry.
  • Role of Humor: How humor is effectively utilized in leadership and team dynamics, especially in remote work environments.
  • Engaging Clients: Strategies for using self-deprecating humor to build stronger client relationships and ease tense situations.
  • Team Deep-Dive Sessions: The importance of candid, deep interactions like the “strengths and weaknesses” and “lifeline” exercises for cultivating team intimacy and trust.
  • Generational Differences: Handling intergenerational communication and finding common ground through shared human values and humor.

Notable Quotes:

  • “Businesses are kind of like organisms… they start to develop their own personality as an entity.”
  • “Humor is a wonderful tool to offset the serious conversations that have to happen when you’re maniacally in pursuit of a big goal.”
  • “My favorite type of humor is typically self-deprecating humor.”
  • “It is a great way … to learn from people and package them up and help some people.”
  • “If you show up and you’re like, ‘I’m going to bring humor to work today,’ it’s probably, what do the kids say? It’s going to be cringe.”


How Humor Can Lead to Success in the C-Suite: Insights from Matt Verlaque

Using Humor to Create a Balanced Work Environment

Effective leadership often involves striking a balance between seriousness and levity, a principle Matt Verlaque lives by. “Nothing’s that serious,” he casually mentions, reflecting on his journey from firefighting to founding a SaaS company. This attitude, however, isn’t about taking work lightly; it’s about recognizing the moments when humor can diffuse tension and foster a more relaxed, productive atmosphere.

The Role of Humor in Serious Contexts

Matt eloquently explains that while the immediate assumption might be that humor and serious business are incompatible, the truth is more nuanced. “We take our performance and the way that we show up for our clients very, very seriously,” he notes, emphasizing that humor isn’t about downplaying the work but about providing balance. “Humor is a wonderful tool to offset the serious conversations that have to happen when you’re maniacally in pursuit of a big goal.”

Humor can act as a societal lubricant, making hard conversations easier and reinforcing bonds within teams. It’s crucial, though, to know when and how to deploy humor. “If you can keep the majors, the majors, and just take that super seriously, then most of the other stuff you can have a lot of fun with,” Matt suggests. This selective seriousness ensures that the gravity of important goals is always clear, while also keeping the overall environment enjoyable and less stressful.

Building Deep Relationships in Remote Teams

One of the significant themes discussed in the podcast is the challenge of using humor to lead in a remote work setup—a challenge Matt and his team navigate adeptly. Remote work can hinder organic relationship-building opportunities that naturally occur in physical office environments, making the strategic incorporation of humor even more critical.

Strengths and Weaknesses Exercise

To bridge the gap, SaaS Academy employs exercises designed to build a profound sense of camaraderie. One such exercise is the “Strengths and Weaknesses,” where team members candidly offer each other feedback. “I would rather make light of a tough lesson I’ve learned than necessarily make light of somebody else’s experience,” Matt says, illustrating the respect and care embedded in such exercises. By sharing personal stories, leaders can make humor an inclusive, bonding experience rather than a divisive one.

The Lifeline Exercise

Another compelling strategy is the “Lifeline” exercise, where team members share the highs and lows of their lives, fostering a deep understanding of each other. “We all left that exercise with a very, very deep understanding of each other,” Matt shares. This level of insight into one another’s lives significantly enriches the team dynamic, leading to organic moments of humor and genuine camaraderie.

These strategic methods ensure that relationships go beyond superficial interactions, allowing humor to naturally integrate into their professional lives. Matt believes that, “when you truly get to know the whole human, as long as you’re not a killjoy yourself, like humor is going to happen.”

Leveraging Self-Deprecating Humor for Rapport

One of the most enlightening revelations from the podcast is Matt’s strategic use of self-deprecating humor. This approach not only makes him more relatable but also creates a safe space for others to open up, which is vital in any coaching or leadership scenario.

Sharing Personal Follies for Professional Gains

Matt exemplifies this through stories of his past mistakes, turning them into learning moments for others. “I learn everything the hard way, usually a couple of times,” he chuckles. He recounts an incident where overhauling a software feature led to an outage that lasted nearly 27 hours, causing significant stress and panic. Despite the ordeal, it became a cautionary tale he often shares, highlighting both the importance of incremental improvements in software development and his willingness to laugh at his own missteps.

The Impact of Self-Deprecating Humor

Self-deprecating humor serves multiple purposes. It humanizes the leader, making them approachable and relatable. It also dispels the notion of infallibility attached to corporate leadership, encouraging team members to communicate openly about their own mistakes and learn from them. “If I can tell a funny story about something that I messed up and position it as a cautionary tale, that’s great,” Matt asserts, reinforcing the idea that humor can be a powerful educational tool.

Wrapping Up the Insights

The conversation with Matt Verlaque is an intricate dance of humor, vulnerability, and insightful leadership strategies. Incorporating humor in leadership is not merely about light-hearted jokes; it’s about creating environments where humor can naturally flourish, driven by deep relationships and understanding among team members.

By strategically using self-deprecating humor, leaders like Matt can bridge gaps, diffuse tensions, and make significant learning moments out of personal follies. Exercises like “Strengths and Weaknesses” and the “Lifeline” not only foster a deep team connection but also provide a fertile ground for organic humor. As Matt rightly points out, “When you’ve done that, you can make it look like it’s not hard. It’s just a different level.”

Ultimately, knowing when and how to inject humor in conversations can catalyze a more harmonious and productive work environment. Such nuanced use of humor ensures that while the significant goals are pursued with earnestness, the journey towards them remains joyful and collaborative. The lesson from Matt’s story is clear: humor is an invaluable tool in leadership, especially when wielded with insight and empathy.

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